Beginner's Guide to Gold-digging: Chapter 2

A Beginner’s Guide to the War at Home

Crispin

Twelve Hours Earlier

I woke up and started my day the way I always like to: with my head between a girl’s legs, tongue sliding over her pussy lips, smelling that sweet, sweet vagina smell and listening to the music of her pleasure. I held onto her breasts with both hands, tweaking her nipples as I worked her clit with my tongue. 

“Cris!” She screamed. “CRIS! I’m- OHHH!”

I was met with a rush of fluid from her sliy, and I drank it like the delicious nectar it was. I lived for this, savored it, reveled in it. And under normal circumstances, I would love it. Unfortunately, this girl I was pleasuring, Sophia, who was lovely and interesting, who had short brown hair and a curvaceous figure and a toned stomach, and whom I’d met at a bar last night, was not the one taking up all the space in my brain, was not the one my imagination was trying to convince me I was banging.

That dubious honor went to Lily DiGiacomo, who I was having evermore trouble not thinking about during lovemaking with each passing day. Shame and self-loathing burned through me when I did it, but it wasn’t enough to make me stop. And Good Lord, I wanted to stop, because obviously she wasn’t interested, obviously it would never happen, OBVIOUSLY that was not a tree I was ever allowed to bark up under any circumstances… But God help me, I couldn’t stop. Ever since I’d laid eyes on those killer abs, gotten a glimpse at her perfect face, caught the sharp end of her wicked tongue, she’d been living in my head at no cost whatsoever. 

God, what is wrong with me? I thought as I tore away the covers I was underneath and gave my latest hookup a wet, messy kiss so she could taste how she felt. I’d spent our initial conversation discerning exactly what drove her wild, and then brought her back to my place to deliver. And it was good. I’d gotten her off a few times before getting there myself, then dove between her legs once more for a bonus round. It was good.

But it wasn’t Lily.

Sophia purred, “That was so great.”

“Glad to hear it,” I said, kissing her cheek. “Want me to make you breakfast?”

“I mean, if it’s not too much trouble.”

“No trouble at all,” I said as I climbed out of bed.

She wolf-whistled at the sight of my bare ass, and I chuckled as I pulled on my boxers and bathrobe. “There’s makeup wipes and floral body wash in the bathroom,” I said as I left my room and entered the house. 

Downstairs a few floors, the house was dark and quiet. The staff hadn’t woken up yet, so it was just me. The bleeding edge of dawn was my favorite time of day, the world getting ready to wake up but not quite able to yet. Gave me time to collect my thoughts, and go about my usual morning routine: I started a pot of coffee, then began chopping up potatoes and peppers and onions while the skillet heated up atop the stove. 

I unskinned a package of sausage and let it sizzle for a few minutes before adding the potatoes and veggies, wafting the delicious, meaty smell of it all. Then, once it was ready, I prepared four small plates: two for Juanita and Carla, our maids, plus two for Trevor and Aaron, our security guards. I then put some more of it into two small tupperwares: one for our cook, Liza, who I’d arranged to always get paid for the full day while letting her sleep until noon, and one for Naomi, my driver. She was the only one of our staff who didn’t live with us- she and her wife had a place on the south shore. Finally, I put aside two more plates: one for me, and one for Sophia. 

“Good morning, Cris,” Juanita yawned as she stepped into the kitchen, already dressed for work. She was a short, portly woman in her late forties with dark brown skin and thickly-coiled natural hair. She and Trevor had been married for most of the time I’d been alive, and they lived on the third floor. I poured her a mug of coffee as she sat at the small round kitchen table.

“Good morning,” I said. “How’d you sleep?”

“Oh, just fine,” she said. “And yourself? I’m assuming not a lot of sleeping occurred?”

“Heh. Maybe.”

“I’m assuming you want the sheets on your bed washed today?”

“Yes, please,” I grinned. 

“Do you think you’ll see this one again?”

“Nah.”

“Why not?” 

“There’s… Someone else who’s caught my eye,” I admitted. 

“Then why isn’t she the one upstairs right now?”

“She’s not interested, trust me,” I shook my head. 

“Well then she’s missing out,” Juanita said. 

“Thanks,” I said with a sad smile as I put the plates and two mugs of coffee onto a tray and started carrying it back towards the stairs. 

“Morning, Cris,” Trevor, a mid-sized white man with a weathered face and a shaved head smiled as he passed me on the stairs. 

“Morning.”

“Any special instructions for your latest overnight guest?”

“Nah, she can see herself out,” I shrugged. “Food and coffee are on the table.”

“Thanks, boss,” he smiled. 

“Please don’t call me that,” I groaned. 

“Sure thing, boss!”

“Ugh,” I rolled my eyes.

Breakfast in bed with Sophia passed without issue, but the conversation dried up pretty quickly. It always went like this: me and my flings never had much in common, and she could probably tell I had other things on my mind. 

Soon enough, she was gone, and I readied myself for work. 

I heated up Naomi’s food in the microwave, poured her coffee into a thermos, and walked outside into the driveway to find the limousine waiting for me. 

Naomi was behind the wheel in her black chauffeur’s uniform, short gray hair neatly parted underneath her black cap. She was in her early sixties and had been driving for our family my entire life. “Morning, Cris,” she smiled as I handed her the food and coffee. 

“Morning, Naomi,” I smiled back. “How’s the wife?”

“Doing fine, just finished a new painting,” Naomi said, pride glimmering off her voice. 

“Nice!” I said. “Hey, if she ever wants to get anything up in a gallery-”

“I know,” Naomi said gently. “And believe me, she does too. But I don’t think she’s after that kind of spotlight.”

I shrugged. “Fair enough.”

She ate quickly, and between mouthfuls said, “So, on-site today?”

“That I am.”

“Hmm.”

“What?”

“I know that smile.”

“I’m smiling?” I asked. 

“You are. In a way I haven’t seen in a long time.”

“Didn’t notice.”

“Uh-huh. What’s her name?”

I chuckled nervously. “I don’t know what you’re talking about.”

She turned on the car and started backing us out of the driveway, away from the four-story wooden mansion and towards the street. Similar mansions stretched out across wide-acred properties on both sides of the street; our neighbors were a lot more willing to show off their wealth than we were going by the renovations they made. Seriously, who the fuck installs a monorail in their backyard?

“Cris, come on, it’s me,” Naomi said as she drove down the street. “There’s clearly a girl. You clearly like her. You’ve been smiling that way ever since you started working this job. Lemme guess: she’s a construction worker? Some giant muscle girl who stole your heart when she beat you at arm wrestling?”

“She would not be able to beat me at arm wrestling,” I said. “She could probably do more sit-ups than me though.”

“Aha! I knew it!” Naomi said. “So she is a construction worker.”

“She’s the forewoman, actually,” I said, taking a drink of my second cup of coffee. “Her name is Lily.”

I saw her grin in the driver’s front mirror. “The way you said her name… Haven’t heard that tone since-”

“Julia Henderson, my senior year of high school,” I finished for her. “Unfortunately, I’m running into the same problem as last time.”

“This one too? Damn, Cris, you’ve gotta stop getting crushes on lesbians. That’s not a good pattern,” she said, laughing at me playfully as we began to enter the actual city. 

“Two times is not a pattern- and hey, Julia said I helped her realize she was gay, so if anything I feel like I did a good thing there. And I’m going to do a good thing here by leaving Lily alone. I mean, I wouldn’t mind being friends with her, but also if I can keep my distance until this stupid crush fades, it’s for the best.”

“Well that’s very responsible of you. I’m proud of you.”

“Thanks,” I beamed. Good old Naomi. Reliable, steady, solid. Don’t know what I’d do without her. 

I waved good-bye as she dropped me off at the site, June Gloom hanging heavily in the sky and giving a cool, wet texture to the air. I walked onto the site, an expanse of hard-hatted workers gathered around a square of cement foundation at the bottom of a dug-out basement… And not really doing anything. 

I waved to Lily’s brother Rob, an average-height, stocky guy with a dark brown buzzcut and the same light tan skin and brown eyes as his sister. He was a couple of years older than me, with a perpetually depressed look on his face that, somehow, looked even more so than usual. 

“Hey,” I said. “What’s going on? Why’s nobody working?”

“We’ve got a neighborhood zoning committee member here, delaying us,” Rob growled. “She’s trying to shut us down.”

“Why? We’re up to code,” I said. 

“She’s just being a petulant asshole, like she always is,” Rob grumbled. 

“Is this someone you know?”

“Not firsthand,” Rob grimaced. “My little sister, though…”

I blinked. “Where’s Lily?”

He pointed across the site. “Tent at the far end. I wouldn’t go in there if I were you, though. Things between Lily and Olivia… It gets wicked bad. Every time. Without fail.”

“I’ll take my chances,” I said. If this was what I thought it was, Lily could use the backup. 

I marched across the lot until I found the tent in question, and was buffeted by a wall of high-pitched shouting before I even made it inside. None of it sounded like Lily. Steeling myself, I pulled open the tent. 

Olivia was, and I hate admitting this, absolutely stunning. She was the same height as me and, by the look of her, the same age as Lily, with long red hair and sharp red nails and plump red lips. She wore a black pencil skirt that stopped just below the knee and accentuated her hips, plus a cream-colored blouse displaying a truly staggering amount of cleavage. 

Both women stared at me like I’d just exploded through a wall. They also looked absolutely furious.

Eyes above the neckline, Winfield. “What’s going on here?”

“Who the fuck is this?” Olivia sneered. She looked at Lily. “Is this what you’re shacking up with nowadays? Wow, great job selling out. Guess everything with you really was a lie.”

Lily balked. “That is not-”

“I’m a representative from the chief investor,” I said. “Now who are you and why are you here?”

She gave a flat look, dripping with self-importance. “Olivia Chesterton. I represent the neighborhood zoning committee. I’m here to make sure this idiot isn’t going to do anything dangerous or illegal.”

“I guarantee you she is not,” I said, my eyes narrowing. “I’ve been here every day since we started, making sure everything is above-board. Lily is the most responsible and effective site manager I’ve ever met.” Granted, she was the only one I’d met, but it seemed prudent to leave that out. 

Olivia met my gaze and her glare intensified, while Lily was standing there with her eyes clamped shut and her bunched fists trembling furiously. 

Olivia’s red lips parted, and I saw something shift behind her eyes. “What’s she doing for you?”

“What does that mean?” I said, barely repressing the acid in my voice. 

“Please, don’t do this,” Lily whispered. 

“Does she go down on you?” Olivia said. “Does she use teeth? Is that why you’re signing off on her bullshit? Why you’re not doing your job? Because that’s just like her.”

My jaw dropped, and a cold, precise fury overtook me. This bitch had the audacity to accuse Lily of not being good at her job? What the actual fuck?! “Okay, let me make this as clear as I possibly can. No fraternizing is going on in this workplace. None. Lily and I aren’t even friends, let alone lovers. In addition to that, you saying all this is sexual harassment-”

“Women can’t commit sexual harassment,” Olivia said with an incredulous wave of her hand and a condescending laugh. “Don’t be ridiculous.”

“And if you don’t cut that shit out immediately, I will sic my company’s lawyers on you,” I said, gritting my teeth. I’d never wanted to punch a woman more than I did right then. “Now, since you’re probably only here to harass your ex-girlfriend-”

“Who told you about that?” Olivia said, grin finally faltering. 

“And you’re doing this out of spite because you can’t actually find any reason to hold up this project, I recommend you leave right the fuck now before I start making some calls.”

Olivia and I spent the next thirty seconds in an unblinking staredown before she… She fucking laughed! “Jesus, it’s worse than I thought.”

“Get out,” I said. 

“She’s not even doing anything for you, you’re just in unrequited love with her! God, that’s pathetic,” Olivia continued. 

“GET OUT!” I screamed.

“Okay, fine,” she kept on laughing, waving at the both of us as she traipsed away. 

I breathed in through my nose and out my mouth as the tent flap fell shut and I turned to face Lily. “Okay, so, what the hell is her-”

“Why would you do that?!” Lily screamed. 

“Um… What?”

“You shouldn’t have done that, you douchebag!” she said, throwing her hands up in the air and pacing back and forth in the tent. “That was not your fight to pick! It was my fight! Mine! You do not get to come in here and white-knight for me, not ever, and especially not when I had it under control!”

“She was walking all over you, being massively unprofessional, and obstructing us from our work,” I said, grinding my teeth again. Fucking hell, DiGiacomo, a little bit of gratitude wouldn’t kill you. “Yes, you clearly had it handled.”

“It’s not your place!” she hissed. “And you don’t know what she’s capable of! Her family is connected. She’s connected. She’s got her fingers in a lot of pies and… Pissing her off just makes things worse. It always does.”

I relaxed my posture and furrowed my brow. From her dilated eyes, haggard breath, and nonstop pacing, it was clear to me she wasn’t actually mad. She was scared. God, what did this girl do to her? And how in Hell could anyone put a woman as strong as this in such a state? 

“Lily,” I said gently. 

“You know what? Just go. Pretty sure we’re still on no eye-contact, and you’re not honoring your end of the deal.”

“I-”

“Go!” she said, pointing at the exit. 

Frustration and pity warred for space inside my mind as I left. And as the day went on, frustration slowly but surely won out. 

Later That Day

Naomi was polite enough not to ask questions while driving me home that evening, which was for the best given vexation was still strangling my brain. I sat there with my head resting on my fist and my leg twitching, staring at the back of the seat in front of me with unblinking anger. 

I had a date that night, one my father had arranged for me, with the daughter of some business colleague of his who he wanted to strengthen our ties to. It had happened a million times, and it was always bullshit. I was supposed to go there after work, but I wasn’t in the mood for the latest facade. It always went the same way: she’d spend about twenty minutes talking about relationships like they were business transactions, at which point I’d bluntly say I’m not actually interested in anything serious, and if she’s up for a fling that’s fine but it’s not going past that. Then she’d looked at me like I’m the most disgusting person in the entirety of New England (every time), and I’d roll my eyes and attempt not to say anything about how I found treating relationships like a job cavalier as fuck (usually with mixed success), and she’d storm off in a huff while calling me an idiot for not wanting to marry a rich girl who’s only desire in life was to become even richer. 

Then I’d go to a bar, pick up a girl who didn’t know me, give her the best night of her life, get off if I was lucky, and then send her on her merry way. Every. Fucking. Time. 

God, even when the sex was good, it was all starting to become so routine, and I knew, I just KNEW that if I got with one of the girls my dad wanted me to marry for the sake of his financial benefit it would be a million times worse. A sterile marriage between two people viewed the whole thing as an extension of their careers. Fucking disgusting. Marriage was a sacred bond between two people in love who’s souls became intertwined with one another, but of course I was just an old-fashioned idiot who didn’t know how things worked in ‘our world.’

That was how it happened. That was how it had always happened. My dad found some other person who was ‘an appropriate match for a Winfield’ and put the pressure on me to speedrun the relationship until we were cranking out grand-babies to add to the will. It was a farce. Completely ridiculous, just like everything else about my dad. 

Well, not tonight. If I went tonight, I would blow up at whoever the girl was.

I stomped up the stairs and locked the door to my room, stripped naked, popped an edible, and started fucking my hand furiously. 

Stupid Lily. Combative, condescending, self-obsessed Lily with her washboard abs and massive jugs hidden underneath all that baggy flannel. Stupid Lily, with her sultry contralto and beautiful brown eyes and plump lips. Stupid, self-assured, self-reliant, fiercely independent, strong-willed Lily!

Thirty minutes into my stroking session, the edible started to kick in, and as the mental barriers in my brain slowly faded away with the blissful lightness of an indica high, she started creeping into my thoughts. I told myself I shouldn’t be thinking about her sitting on my lap and gripping my cock while playing tonsil-hockey with me, that that was a dangerous train of thought to board, that she was off-limits, but the more I told myself that, the closer I started to get towards orgasm. 

Stupid sexy Lily… 

My phone rang. 

“Fuck!” I shouted as the ringtone (Bone Machine by the Pixies) started blaring from the source on my nightstand. I was so close, even as anger and shame and self-loathing flagellated me. I kept stroking as the ringtone faded… And then it immediately started again. 

And again. 

AND AGAIN.

“Ahhh!” I yelled as I finally let go of my dick and grabbed the phone. 

It was my dad. Of course it was. 

I opened the phone and put it on speaker phone as I grinded my teeth, thoughts of certain short-haired, curvy, shockingly fit Italian girl continually intruding. 

“Crrrrrrrrrrriiiiiiiisssssssppppppppppiinnnnnnnnn!!!!” my father yelled. I don’t even know why I specified that- he yelled everything. 

“What?” I monotoned.

“Don’t you take that monotonous tone with me, young man! Do you know nothing of the embarrassment you’ve caused me?! The DISHONOR you have brought upon our noble house?! The UTTER RUINATION your continued DEPRAVITY threatens us with!?” 

I could picture him pacing back and forth, hands flying about, a million attendants cowering in fear around him while he spoke. This was normally the part where I laughed and gave some sarcastic reply, pretended to apologize, and said it won’t happen again. But I couldn’t think of anything. All I could think about was Lily. Lily kissing my neck and giving me a hickey. Lily teasing me and toying with me. Lily screaming at me. Dammit!

“Oh, get over it,” I said. 

“Exxccuuuuuussssseeee meeee?!” Dad bellowed. 

“You heard me. I didn’t go on a blind date. So what?” I said, not sure if it was the weed or the sexual frustration talking. 

“So your continued obstinance is a hindrance to our EMPIYAH!” 

I scoffed. “We don’t have an empire. We’re just rich. That’s it!”

“Wealth is EMPIYAH, son! How many times must I impart upon you that knowledge! And your refusal to enter a more sacred union-”

“It’s not a sacred union if the whole thing is a sham.” Stupid Lily, beautiful Lily, perfectly fucked-up Lily…

“And why would it be a sham!? And do not utter the words ‘it just wasn’t a good fit!’ Every time you say that it becomes less convincing. So tell me, mine eldest boy-child, what on earth was so wrong with this one that you didn’t even bother to GRACE HER WITH YOUR PRRRRRRRESSSENCE!”

“She wasn’t Lily!” I yelled. 

And the high was immediately snuffed out. My eyes widened and I cringed. Oh God, I said that out loud. Oh fuck-

“And whomst, PRAY TELL, is Lily?”

“She’s, uh, she’s…,” okay c’mon Winfield, say something, say anything, literally anything- “She’s the girl I’m seeing.”

“H-WHHHATTT?! You think that one of your latest flagrant displays of debauchery is a good reason to-”

“She’s not- it’s more serious than that-”

“How serious?”

An image popped into my head, of Lily in a white dress she’d probably sneer at, and I guess the weed hadn’t fully worn off after all, because I said, “She’s my fiance.”

“...”

I blinked. “Dad?”

“...”

“Dad, are you still there?”
“Son,” Dad said softly. Oh, that was bad. I hadn’t heard him speak softly in… Uh… Long enough I didn’t remember when it last happened. “You are betrothed? Truly?”

Don’t say it- “Yes.”

“Well! This changes everything! I know I would prefer for you to marry strategically, but I suppose you have always been a romantic at heart and marrying for love no doubt has a whimsical appeal to you,” Dad said, still speaking with that terrifyingly calm tone. 

Don’t say it don’t say it- “I mean… Yeah, that’s the long and short of it.”

“But hhhwhy haven’t you told me of this young Lilian erstwhile?”

Don’t say it don’t say it don’t say it… Actually seriously DON’T FUCKING SAY IT- “I didn’t think you’d approve.” FUCK!

“Whyever not?!”

Well, best lies are the truth. And this wasn’t really a topic that had ever come up, so… “Because you’re not very open-minded, Dad. You’re unenlightened.”

“Hhhhwwwwhhhhhattttever do you mean? I pride myself on the strong tradition of New England intellectualism! Why on earth would I not be open-minded enough?”

“You’re just not, trust me,” I said, the pit in my stomach expanding more and more.

“Then I shall endeavor to prove you wrong! I must meet this fiance, this Lily, of yours!”

“I really don’t think that’s necessary-”

“It’s PARAMOUNT! I shall fly home immediately! I expect to meet her tomorrow night!”

“What?!” I said, my shoulders slumping. 

“Oh, and my son, my namesake, fruit of my loins, should I discover that there is no Lily, that this was all a ruse, and that you are simply making excuses and continuing your petulant defiance of your familial obligations into your third decade, I shall have no choice but to take drastic measures. I will cut you off if I find out you are lying. Do I make myself clear?”

For the love of God don’t say it- “Yes, sir.”

“Good. Sleep well, my son. I look forward to meeting my future daughter-in-law tomorrow night. I’m sure your mother will be thrilled.”

I groaned. “Karen is not my mother! She’s just some gold-”

He hung up before I could finish, and I fell backwards into my bed, grabbed a pillow and screamed into it.